# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_6736
_database_code_depnum_ccdc_archive 'CCDC 2070113'
loop_
_audit_author_name
_audit_author_address
'xinjie Li'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;
_audit_creation_date             2020-11-27
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H11 Cl N4 S'
_chemical_formula_sum            'C9 H11 Cl N4 S'
_chemical_formula_weight         242.73
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.0066(4)
_cell_length_b                   12.2115(7)
_cell_length_c                   18.0086(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.708(9)
_cell_angle_gamma                90.00
_cell_volume                     1100.53(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1720
_cell_measurement_temperature    113.60(10)
_cell_measurement_theta_max      29.1430
_cell_measurement_theta_min      4.3920
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4424
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      113.60(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8516
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   55.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335 -178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335    0.0000  -60.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   19.0000 -180.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1083472000
_diffrn_orient_matrix_UB_12      -0.0027033000
_diffrn_orient_matrix_UB_13      -0.0262179000
_diffrn_orient_matrix_UB_21      -0.0576263000
_diffrn_orient_matrix_UB_22      -0.0429814000
_diffrn_orient_matrix_UB_23      0.0206335000
_diffrn_orient_matrix_UB_31      -0.0710180000
_diffrn_orient_matrix_UB_32      0.0389757000
_diffrn_orient_matrix_UB_33      0.0208980000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1870
_reflns_number_total             2161
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0308P)²+0.3298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19060(9) 0.40829(4) 0.75446(3) 0.01967(15) Uani 1 1 d . . .
Cl1 Cl 0.30326(11) 0.87104(4) 1.00755(3) 0.02666(16) Uani 1 1 d . . .
C2 C 0.4584(4) 0.78852(16) 0.94372(11) 0.0194(4) Uani 1 1 d . . .
N2 N 0.7056(3) 0.66583(13) 0.83499(9) 0.0191(4) Uani 1 1 d . . .
N1 N 0.6516(3) 0.83267(13) 0.90506(9) 0.0204(4) Uani 1 1 d . . .
N4 N 0.1899(3) 0.61335(13) 0.96399(9) 0.0209(4) Uani 1 1 d . . .
C1 C 0.7657(4) 0.76906(16) 0.85374(11) 0.0214(5) Uani 1 1 d . . .
H1 H 0.9039 0.8011 0.8281 0.026 Uiso 1 1 calc R . .
C8 C 0.1643(4) 0.53565(16) 0.70315(12) 0.0234(5) Uani 1 1 d . . .
H8A H 0.0131 0.5306 0.6684 0.028 Uiso 1 1 calc R . .
H8B H 0.1273 0.5942 0.7377 0.028 Uiso 1 1 calc R . .
N3 N 0.3993(3) 0.52330(12) 0.87275(9) 0.0164(4) Uani 1 1 d . . .
C7 C 0.5385(4) 0.32979(16) 0.86014(12) 0.0241(5) Uani 1 1 d . . .
H7A H 0.3854 0.3025 0.8851 0.036 Uiso 1 1 calc R . .
H7B H 0.6809 0.3433 0.8958 0.036 Uiso 1 1 calc R . .
H7C H 0.5952 0.2766 0.8247 0.036 Uiso 1 1 calc R . .
C4 C 0.5100(4) 0.62626(15) 0.87576(11) 0.0162(4) Uani 1 1 d . . .
C9 C 0.4116(4) 0.56626(17) 0.66022(12) 0.0260(5) Uani 1 1 d . . .
H9A H 0.5543 0.5855 0.6946 0.039 Uiso 1 1 calc R . .
H9B H 0.3711 0.6275 0.6284 0.039 Uiso 1 1 calc R . .
H9C H 0.4649 0.5050 0.6307 0.039 Uiso 1 1 calc R . .
C6 C 0.4651(4) 0.43637(15) 0.82001(11) 0.0171(4) Uani 1 1 d . . .
H6 H 0.6195 0.4602 0.7920 0.020 Uiso 1 1 calc R . .
C5 C 0.2100(4) 0.52154(16) 0.92663(11) 0.0197(4) Uani 1 1 d . . .
H5 H 0.1052 0.4604 0.9358 0.024 Uiso 1 1 calc R . .
C3 C 0.3780(4) 0.68086(15) 0.93231(11) 0.0171(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0169(3) 0.0230(3) 0.0191(3) -0.0035(2) -0.0002(2) -0.0008(2)
Cl1 0.0367(3) 0.0198(3) 0.0236(3) -0.0040(2) 0.0035(2) 0.0002(2)
C2 0.0229(10) 0.0183(10) 0.0169(10) -0.0006(8) -0.0028(8) 0.0018(8)
N2 0.0179(8) 0.0209(8) 0.0186(9) 0.0041(7) 0.0013(7) -0.0018(7)
N1 0.0223(9) 0.0193(8) 0.0195(9) 0.0029(8) -0.0023(7) -0.0034(7)
N4 0.0234(9) 0.0222(9) 0.0175(9) -0.0004(7) 0.0043(7) -0.0048(7)
C1 0.0187(10) 0.0241(11) 0.0214(11) 0.0070(9) -0.0002(8) -0.0053(8)
C8 0.0203(10) 0.0264(11) 0.0236(11) -0.0017(9) 0.0003(9) 0.0072(9)
N3 0.0178(8) 0.0177(8) 0.0139(8) -0.0008(7) 0.0022(7) -0.0040(7)
C7 0.0288(11) 0.0203(10) 0.0231(11) -0.0007(9) -0.0038(9) 0.0000(9)
C4 0.0160(9) 0.0177(10) 0.0147(10) 0.0026(8) -0.0022(8) -0.0021(8)
C9 0.0261(11) 0.0280(11) 0.0239(12) 0.0038(10) 0.0030(9) 0.0050(9)
C6 0.0179(10) 0.0166(10) 0.0168(10) -0.0017(8) 0.0007(8) -0.0015(8)
C5 0.0214(10) 0.0203(10) 0.0174(10) 0.0004(9) 0.0028(8) -0.0063(8)
C3 0.0192(10) 0.0178(10) 0.0142(9) 0.0014(8) -0.0002(8) -0.0012(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.812(2) . ?
S1 C6 1.818(2) . ?
Cl1 C2 1.730(2) . ?
C2 N1 1.323(2) . ?
C2 C3 1.389(3) . ?
N2 C1 1.337(2) . ?
N2 C4 1.332(2) . ?
N1 C1 1.347(3) . ?
N4 C5 1.313(2) . ?
N4 C3 1.387(2) . ?
C1 H1 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.525(3) . ?
N3 C4 1.375(2) . ?
N3 C6 1.468(2) . ?
N3 C5 1.376(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 C6 1.528(3) . ?
C4 C3 1.400(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 H6 0.9800 . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C6 102.20(9) . . ?
N1 C2 Cl1 117.51(14) . . ?
N1 C2 C3 121.42(17) . . ?
C3 C2 Cl1 121.05(15) . . ?
C4 N2 C1 111.50(17) . . ?
C2 N1 C1 117.22(16) . . ?
C5 N4 C3 103.51(16) . . ?
N2 C1 N1 128.32(18) . . ?
N2 C1 H1 115.8 . . ?
N1 C1 H1 115.8 . . ?
S1 C8 H8A 108.5 . . ?
S1 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 S1 114.90(14) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C4 N3 C6 126.06(15) . . ?
C4 N3 C5 105.78(15) . . ?
C5 N3 C6 128.11(15) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
N2 C4 N3 127.76(17) . . ?
N2 C4 C3 126.82(18) . . ?
N3 C4 C3 105.41(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S1 C6 H6 108.3 . . ?
N3 C6 S1 112.11(13) . . ?
N3 C6 C7 111.43(16) . . ?
N3 C6 H6 108.3 . . ?
C7 C6 S1 108.23(13) . . ?
C7 C6 H6 108.3 . . ?
N4 C5 N3 114.37(17) . . ?
N4 C5 H5 122.8 . . ?
N3 C5 H5 122.8 . . ?
C2 C3 C4 114.67(17) . . ?
N4 C3 C2 134.39(18) . . ?
N4 C3 C4 110.93(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C2 N1 C1 -177.88(14) . . . . ?
Cl1 C2 C3 N4 -2.8(3) . . . . ?
Cl1 C2 C3 C4 176.14(14) . . . . ?
C2 N1 C1 N2 1.5(3) . . . . ?
N2 C4 C3 C2 2.4(3) . . . . ?
N2 C4 C3 N4 -178.44(18) . . . . ?
N1 C2 C3 N4 178.9(2) . . . . ?
N1 C2 C3 C4 -2.2(3) . . . . ?
C1 N2 C4 N3 -179.01(19) . . . . ?
C1 N2 C4 C3 -0.7(3) . . . . ?
C8 S1 C6 N3 64.87(14) . . . . ?
C8 S1 C6 C7 -171.83(14) . . . . ?
N3 C4 C3 C2 -178.99(16) . . . . ?
N3 C4 C3 N4 0.2(2) . . . . ?
C4 N2 C1 N1 -1.4(3) . . . . ?
C4 N3 C6 S1 -111.37(18) . . . . ?
C4 N3 C6 C7 127.15(19) . . . . ?
C4 N3 C5 N4 -0.3(2) . . . . ?
C6 S1 C8 C9 62.05(17) . . . . ?
C6 N3 C4 N2 -3.8(3) . . . . ?
C6 N3 C4 C3 177.59(17) . . . . ?
C6 N3 C5 N4 -177.75(18) . . . . ?
C5 N4 C3 C2 178.6(2) . . . . ?
C5 N4 C3 C4 -0.3(2) . . . . ?
C5 N3 C4 N2 178.65(19) . . . . ?
C5 N3 C4 C3 0.0(2) . . . . ?
C5 N3 C6 S1 65.7(2) . . . . ?
C5 N3 C6 C7 -55.8(2) . . . . ?
C3 C2 N1 C1 0.5(3) . . . . ?
C3 N4 C5 N3 0.4(2) . . . . ?

